Production of alkylated phenols



Patented 8, 1931 UNITED STATES PATENT OFFICE LITZ, AND REINHARD CLERC, 0F BERLIN, KAHLBAUM A.-G., 0F BERLIN, GERMANY GERMANY, ASSIGNORS TO SCHERING- PRODUCTION OF ALKYLATED PHENOLS No Drawing. Application filed June 29, 1928, Serial Ho. 289,823, and in Germany July 21, 1927.

Our invention refers to the manufacture of alkylated phenols,

The process of manufacture of this invention is by heating an alkyl ether of a phenol or a derivative thereof under pressure to an elevated temperature, in the presence, if desired, of a catalyst, it being understood that the invention deals with saturated alkyl groups. Under these conditions alkyl ethers of phenols undergo a transformation in such a manner that the alkyl migrates into the nucleus in the sense of the following formulae OR on As secondary products are also obtained poly-substituted phenols in accordance with the following equation OR on on The following examples illustrate the invention Ewamplel Phenyl-ethyl-ether is heated in a shaking autoclave to 280-320 C. After some hours the process is interrupted and para-ethylphenol is obtained together with small quantities of di-ethyl-phenol and phenol.

Example 2 isopropyl-phenol (thymol2 C. in a shaking autoclave in the mospheres. After some hours the process is interrupted and there is obtained a mixture of 3-methyl-6-isopropyl-phenol (thymol) with 3-methyl-4-isopropyl-phenol from which the valuable thymol can be separated in the known manner.

Emample 3 Phenyl-cyclohexyl-ether is treated as described in Example 2. Para-cyclohexylphenol is obtained. The process can also be applied to derivatives of the phenol ethers as, for example, halogen derivatives, whereby the result can be attained that the alk l-group migrating into the nucleus can be irected to a predetermined position.

Various changes may be made in the details disclosed in the foregoing specification without departing from the invention or sacrificing the advantages thereof.

In the following claims the term phenol is meant to cover also halogen or alkyl-derivatives of phenol.

We claim:

1. The process of producing an alkylated phenol with a saturated alkyl up comprising heating under pressure t e ether of a phenol with a saturated aliphatic alcohol.

2. The process of producing an alkylated' henol with a saturated alkyl group comprismg heatin under pressure the ether of a phenol wit 1 a. saturated aliphatic alcohol, in the presence of contact masses of high porosity.

3. The process of producing 3-meth l-6- comprising eating the lso-propyl-ether o meta-cresol under pressure.

4. The process of producing 3-methyl-6- isopropylhenol (thymol) comprising heating the iso-propylether of meta-cresol' under pressure in the presence of contact masses avin a hi h orosit a g g VALTR SCHOELLER. HANS JORDAN.

REINHARD CLERG.

hereupon the pressure rises to about at 

